Why'd You Think You Could Do That?

Most people wait to “feel” brave. But what if that’s the wrong game entirely?
In this Bravery Digest, Sam Penny breaks down why you don’t rise to the level of your motivation — you fall to the level of your environment. Motivation fades. Willpower runs dry. But if you build the right systems, routines and surroundings, bravery becomes inevitable.
This short, sharp solo episode gives you five tactical ways to build an environment where bold action becomes your default, not the exception. If you want to stop waiting and start showing up braver — even on the hard days — this one’s for you.
🧠 In This Episode:
  • Why motivation is overrated and unreliable
  • The truth about willpower and comfort
  • 5 ways to engineer a braver environment:
    1. Physical cues that trigger bravery
    2. Accountability you can’t escape
    3. Removing easy outs that lead to comfort
    4. Raising the room and upgrading your circle
    5. Automating bravery with repeatable habits
  • Plus: a preview of Thursday’s full interview with blind endurance athlete and adventurer Gerrard Gosens, who lives and breathes these principles.
🔗 Resources & Mentions:
🎙 Host: Sam Penny
Coach for the brave. Ultra-endurance athlete. Business builder. Helping people turn bold goals into daily action.
Follow on Instagram/TikTok: @90dayswithsam
Book a call: https://sampenny.com/chat

Creators and Guests

Host
Sam Penny
Sam Penny is an adventurer, entrepreneur, and keynote speaker who lives by the mantra “Say YES! to the Impossible.” From swimming the English Channel in winter to building and selling multi-million-dollar companies, Sam thrives on pushing boundaries in both business and life. As host of Why’d You Think You Could Do That?, he sits down with ordinary people who have done extraordinary things, uncovering the mindset, resilience, and bold decisions that made it possible — and showing listeners why their own impossible is closer than they think.

What is Why'd You Think You Could Do That??

They’ve swum oceans, scaled mountains, launched empires, and shattered expectations. But before they did any of it, someone, maybe even themselves, thought: “You can’t do that.”

Hosted by Sam Penny, Why’d You Think You Could Do That? dives into the minds of people who said “screw it” and went for it anyway. From adventurers and elite athletes to wildcard entrepreneurs and creative renegades, each episode unpacks the one question they all have in common:

“Why'd you think you could do that?”

If you’re wired for more, haunted by big ideas, or just sick of playing it safe, this is your show.

Sam Penny (00:00)
Welcome back to the bravery digest on why do you think you could do that podcast? I'm Sam Penny coach for the brave. Today, let's talk about something that most people get dead wrong. Why your environment, not your motivation is what really determines how brave you'll be. Let's get real for a second.

You don't rise to the level of your motivation. You fall to the level of your environment and willpower is overrated. Hype only lasts until you hit your first obstacle. If you want to act braver consistently, you need to design an environment where bravery is the default, not the exception. Because here's the truth, comfort is always available. If you don't deliberately build systems that push you forward,

you'll unconsciously slide back every single time. So how do you create an environment that demands your best, even on days when you don't feel like showing up? Let's get tactical. Here's five elements to build a brave environment that will stretch you, challenge you and force you to grow. First one is to build physical cues that trigger bravery. Surround yourself with reminders of who you're becoming, not just

who you've been put your 90 day goal up on the wall. Pin a note that says move before fear and keep your bravery audit visible right beside your screen if you need to let your physical space shape your mental state. Now the second thing accountability you can't wiggle out of. Don't just talk about your goals, raise the stakes, announce deadlines publicly.

Put some money on the line. someone to to it and actually Bravery thrives when there are real consequences for playing small. Number three, remove the easy outs. Make it harder to shrink back to comfort. Delete your fallback plan. Block your usual distractions. Lock time into your calendar for

discomfort driven work. Make the brave thing the only thing.

Number four, raise the room. Who you surround yourself with sets the standard. Join a group where bold moves are normal. Work with a coach who doesn't let you coast. Be around people who make your current level feel uncomfortable. And remember, small circles mean small thinking. Number five, build habits that run without motivation.

Set bravery to run on autopilot. That could be one 90 second brave action every day, a Friday journal, what scared me this week, or a weekly review of where you hid and where you showed up. Systems outperform motivation every single time. Here's the big takeaway. Bravery isn't about hype or waiting to feel ready.

It's about building conditions that demand better, where excuses get crowded out and your best self gets called up day after day. So here's my challenge for you. What's one change you'll make to your environment this week to demand more from yourself?

Maybe it's as simple as writing your brave goal on the wall. Maybe it's joining a group or putting a little money on the line. Pick one and put it in play today. Let's stop hoping to feel brave. Let's build the space that requires it. Now, before I wrap, I want to see up a guest who personifies everything we've just talked about. Someone who built his environment and his entire life to

demand the extraordinary. This Thursday, I'll be sitting down with Jared Gossens, blind since birth, elite athlete, business owner and a man who has made the impossible look routine. If you want to know what it looks like to build a life that requires bravery, don't miss this episode. I'm Sam Penny, coach for the brave. Thanks for listening to the bravery digest. Go build your brave environment and see what you're really capable of.

I'll see you this Thursday.